Sailboating

When a man places a strap on backwards as to be able to have sex with two women. The women straddle him from alternate sides while linking hands over the mans shoulders creating a triangle shape. When the legs and as are both linked the man stands creating the shape of a mast and sail. He then has sex with the two women.

I need to work on my leg strength if I want to do some sailboating tomorrow night

by Mypenisisapizza November 23, 2014

Shitposting

What you are watching right now.

I love the mountain goats shitposting 2: electric boogaloo.

by ClassicJLimbo March 17, 2017

sailboating

Sailboating is the act of very very very slowly dragging and flaccid penis across someone's face.

"I love sailboating with my boyfriend. it's the softest 5 minutes of my life."

by allthemarbles June 1, 2015

Sailboating

When one partner spreads the other partners scrotum with both hands forming a "sail", then performs a raspberry by blowing on the scrotum with lips pursed thus creating vibrations.

Jason: If I fall asleep and start snoring, wake me up and I'll go to bed.
Travis: Yeah you'll wake up to me Sailboating you!
Jason: don't you mean.....nah nevermind.

by Greenhower January 22, 2016

Sailboating

As opposed to the pedestrian act of motorboating, sailboating, shuts off the motor and gets back to nature. First, you drop anchor in preparation for a little sunset rose and cheese. The captain puts his or her face down between the butt cheeks. Whilst the first mate uncorks the wine and cuts the cheese, you just let the wind blow across your face and through your hair enjoying all that nature has to offer.

Chad took up Thadeus on his offer to go sailboating...they had a great time!

by chappynyc September 20, 2018

Shitposting

Using social media while on the toilet

My constitutional is slow so I’m multitasking by shitposting.

by Bee Vomit October 29, 2020

Sailboating

Same concept as a motorboating (where you bury your face between a pair of boobs and vigorously shake your head from side to side) except sailboating is slower so you can take it the view.

I wanted to motorboat the girl, but her bazongas were so nice that I opted to slow down and ended up sailboating her instead.

by Lake Partiers May 4, 2021